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Jamaica

$98+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated July 31, 2025.

Round-trip from

$347
(SmartFares)

One-way from

$117
(Booking.com)

Popular in

March

Cheapest in

February

Average price

$599

Good round-trip deal

$501 or less

Good one-way deal

$186 or less
From Chicago (CHI) to Jamaica
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One-way flight from Chicago (CHI) to Jamaica
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Highest demand for flights based on searches. 2% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
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Price to beat on a one-way flight from Chicago (CHI) to Jamaica.
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Find flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:44 pmORD - KIN
1 stop16h 18mSpirit Airlines
Wed 10/112:08 pmKIN - ORD
1 stop10h 40mSpirit Airlines
Deal found 7/29$335
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:20 amORD - KIN
1 stop12h 40mDelta
Tue 9/239:00 amKIN - ORD
1 stop13h 14mDelta
Deal found 7/29$375
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:15 amMDW - MBJ
1 stop6h 30mFrontier
Sun 9/212:12 pmMBJ - MDW
1 stop9h 08mFrontier
Deal found 7/29$381
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:05 amORD - MBJ
1 stop6h 00mSpirit Airlines
Fri 10/1012:10 pmMBJ - ORD
1 stop22h 33mSpirit Airlines
Deal found 7/29$381
This CheapOair deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/158:12 pmORD - MBJ
1 stop15h 02mMultiple Airlines
Mon 8/189:05 amMBJ - ORD
1 stop15h 17mMultiple Airlines
Deal found 7/30$383
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/135:22 amORD - MBJ
1 stop10h 00mAmerican Airlines
Tue 10/212:30 pmMBJ - ORD
1 stop6h 52mAmerican Airlines
Deal found 7/30$384
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/135:50 amMDW - MBJ
1 stop7h 45mSouthwest
Thu 10/1612:20 pmMBJ - MDW
1 stop8h 15mSouthwest
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:30 amORD - MBJ
1 stop7h 39mDelta
Thu 9/251:25 pmMBJ - ORD
1 stop8h 00mDelta
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/216:00 amMDW - MBJ
1 stop9h 34mDelta
Thu 9/251:25 pmMBJ - MDW
2 stops19h 15mDelta
Deal found 7/29$389
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:10 amORD - MBJ
1 stop7h 35mFrontier
Sun 9/212:12 pmMBJ - ORD
1 stop9h 58mFrontier
Deal found 7/29$399
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:00 amMDW - KIN
1 stop14h 25mDelta
Sun 9/149:00 amKIN - MDW
1 stop12h 36mDelta
Deal found 7/29$493
This Mytrip deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:15 amMDW - KIN
3 stops31h 55mMultiple Airlines
Wed 9/36:25 pmKIN - MDW
2 stops18h 38mMultiple Airlines
Deal found 7/29$827

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Chicago

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Tue 9/16

6:44 pm-11:02 am

1 stop16h 18m

Kingston Norman Manley

Wed 10/1

12:08 pm-10:48 pm

1 stop10h 40m

$335

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 9/18

5:30 am-8:00 pm

1 stop14h 30m

Kingston Norman Manley

Sun 9/21

9:00 am-11:54 pm

1 stop14h 54m

$375

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sat 9/20

6:15 am-12:45 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sun 9/21

2:12 pm-11:20 pm

1 stop9h 08m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sat 10/4

5:05 am-11:05 am

1 stop6h 00m

Montego Bay Sangster Intl

Fri 10/10

12:10 pm-10:43 am

1 stop22h 33m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 8/15

8:12 pm-11:14 am

1 stop15h 02m

Montego Bay Sangster Intl

Mon 8/18

9:05 am-12:22 am

1 stop15h 17m

$383

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 10/13

5:22 am-3:22 pm

1 stop10h 00m

Montego Bay Sangster Intl

Tue 10/21

2:30 pm-9:22 pm

1 stop6h 52m

$384

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Mon 10/13

5:00 am-1:55 pm

1 stop8h 55m

Montego Bay Sangster Intl

Thu 10/16

12:50 pm-8:40 pm

2 stops7h 50m

$385

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 9/22

5:30 am-1:09 pm

1 stop7h 39m

Montego Bay Sangster Intl

Thu 9/25

1:25 pm-9:25 pm

1 stop8h 00m

$385

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 9/21

6:00 am-3:34 pm

1 stop9h 34m

Montego Bay Sangster Intl

Fri 9/26

4:59 pm-12:28 pm

2 stops19h 29m

$389

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Fri 9/19

5:10 am-12:45 pm

1 stop7h 35m

Montego Bay Sangster Intl

Sun 9/21

2:12 pm-12:10 am

1 stop9h 58m

$399

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 26 results
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Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $562). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Chicago to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated July 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
WestJet
7.2
Good
2,978 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,049 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $117 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $161 and American Airlines from $164 one-way.

  • What are the most popular routes from Chicago to Jamaica?

    The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $658 for a flight from Chicago to Jamaica. The cheapest flight overall is $164 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $282.

  • Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

    Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

  • Can I find deals for business class flights from Chicago to Jamaica?

    Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $562). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
Midway to Montego Bay flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Willemstad flights
St. Louis to Luis Munoz Marin Intl flights
Midway to Punta Cana flights
O'Hare Intl to Santo Domingo flights
St. Louis to Punta Cana flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
O'Hare Intl to Simpson Bay flights
St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Bridgetown flights
Midway to Saint Thomas Island flights
St. Louis to Saint Thomas Island flights
St. Louis to Nassau flights
O'Hare Intl to Ponce flights
Midway to Providenciales flights
Midway to Santo Domingo flights
O'Hare Intl to Christiansted flights
St. Louis to Oranjestad flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
Moline to Punta Cana flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Simpson Bay flights
Midway to Simpson Bay flights
O'Hare Intl to Port of Spain flights
Midway to George Town flights
St. Louis to Willemstad flights
St. Louis to Georgetown flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to St. George's flights
St. Louis to Santo Domingo flights
O'Hare Intl to Road Town flights
St. Louis to George Town flights
Peoria to Luis Munoz Marin Intl flights
Moline to Luis Munoz Marin Intl flights
Moline to Saint Thomas Island flights
St. Louis to Providenciales flights
Midway to Castries flights

Top 5 airlines flying from Chicago to Jamaica

Discover the top 5 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$433FlexibilityNo cancel feeOn-time65%
DeltaCheapest$295Average$817FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$410Average$622FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$432Average$683FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$555Average$724FlexibilityNo cancel feeOn-time63%

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